JPH0213A - Composition for forming protective film for transparent electrode of liquid crystal display element - Google Patents
Composition for forming protective film for transparent electrode of liquid crystal display elementInfo
- Publication number
- JPH0213A JPH0213A JP20034088A JP20034088A JPH0213A JP H0213 A JPH0213 A JP H0213A JP 20034088 A JP20034088 A JP 20034088A JP 20034088 A JP20034088 A JP 20034088A JP H0213 A JPH0213 A JP H0213A
- Authority
- JP
- Japan
- Prior art keywords
- protective film
- composition
- transparent electrode
- liquid crystal
- crystal display
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 230000001681 protective effect Effects 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 title claims description 30
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- -1 polysiloxane Polymers 0.000 claims abstract description 13
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract 4
- 150000002902 organometallic compounds Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000011253 protective coating Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 8
- 238000010438 heat treatment Methods 0.000 abstract description 7
- 239000011248 coating agent Substances 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 abstract description 5
- 230000007547 defect Effects 0.000 abstract description 5
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 239000005054 phenyltrichlorosilane Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000270708 Testudinidae Species 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- UARGAUQGVANXCB-UHFFFAOYSA-N ethanol;zirconium Chemical compound [Zr].CCO.CCO.CCO.CCO UARGAUQGVANXCB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HSXKFDGTKKAEHL-UHFFFAOYSA-N tantalum(v) ethoxide Chemical compound [Ta+5].CC[O-].CC[O-].CC[O-].CC[O-].CC[O-] HSXKFDGTKKAEHL-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/133345—Insulating layers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
Abstract
Description
【発明の詳細な説明】
《産業上の利用分野》
一本発明は液晶表示素子の透明電極保護被膜形成用組成
物に関し、さらＫ詳しくは低温で乾燥硬化することがで
きる液晶表示素子の透明電極保護被膜形成用組成物およ
びこれを用いた液晶表示素子Ｋ関する。Detailed Description of the Invention <<Industrial Application Field>> 1. The present invention relates to a composition for forming a protective film for a transparent electrode of a liquid crystal display element, and more particularly, a composition for forming a transparent electrode of a liquid crystal display element that can be dried and cured at a low temperature. The present invention relates to a composition for forming a protective film and a liquid crystal display element K using the composition.
（従来の技術）
従来、液晶表示素子の製造に際しては、パターニングさ
れた透明電極を有する基板Ｋ、ポリイミド等の有機高分
子からなる配向膜を塗布形成し。(Prior Art) Conventionally, when manufacturing a liquid crystal display element, a substrate K having a patterned transparent electrode and an alignment film made of an organic polymer such as polyimide are formed by coating.
配向処理を行なった後、素子を組み立てる方法が用いら
れていた。しかし、近年、液晶表示素子の大型化Ｋ伴い
、配向膜のピンホールや素子のギャップ中に混入した異
物が、配向膜をキズっけたシ。A method has been used in which the device is assembled after alignment treatment. However, in recent years, as liquid crystal display elements have become larger, foreign substances that have entered pinholes in the alignment film or gaps between the elements have caused damage to the alignment film.
つき破ることＫよって起こる上下基板間の導通Ｋよる表
示不良が問題となっている。Display defects due to conduction K between the upper and lower substrates caused by punching and tearing have become a problem.
最近では、これを解決する手段として、透明電極と配向
膜の間ｋ絶縁性の層を形成する方法が検討され、例えば
、（１）スパッタリングＫよる低温で酸化膜を形成する
方法、（２）アルコキシシラン、アルコキシチタンおよ
び増粘剤として有機高分子を含む溶液を印刷法等で塗布
した後、熱処理して酸化膜とする方法等が採用されてい
る。Recently, as a means to solve this problem, methods of forming an insulating layer between the transparent electrode and the alignment film have been studied.For example, (1) a method of forming an oxide film at a low temperature by sputtering, (2) A method has been adopted in which a solution containing alkoxysilane, alkoxytitanium, and an organic polymer as a thickener is applied by a printing method or the like, and then heat-treated to form an oxide film.
しかしながら、（ｌ）の方法では、真空系の高価な装置
が必要であシ、パッチ処理の九め生産性が悪く、また【
２）の方法では、酸化膜とするために高温処理が必要で
あり、この高温処理Ｋよって透明電極のシート抵抗値が
上昇してしまう等の欠点があった。However, method (l) requires expensive vacuum equipment, has poor patch processing productivity, and
Method 2) requires high-temperature treatment to form an oxide film, and has drawbacks such as the high-temperature treatment K increasing the sheet resistance of the transparent electrode.
（発明が解決しようとする課題）
本発明の目的は、前記技術の欠点を解決し、低温の熱処
理で硬化し、透明電極のシート抵抗値が上昇しない優れ
た透明電極の保護被膜を形成することができる液晶表示
素子の透明電極保護被膜形成用組成物および透明電極の
保護被膜Ｋこれを用いた液晶表示素子を提供することＫ
ある。(Problems to be Solved by the Invention) An object of the present invention is to solve the drawbacks of the above-mentioned techniques and to form an excellent protective coating for a transparent electrode that is cured by low-temperature heat treatment and does not increase the sheet resistance of the transparent electrode. A composition for forming a protective film for a transparent electrode of a liquid crystal display element and a protective film for a transparent electrode K.Providing a liquid crystal display element using the same.
be.
《課題を解決するための手段》
本発明者らは、鋭意検討した結果、＊定の末端ヒドロキ
シラダーポリシロキサンおよび特定の有機金属化合物を
溶剤Ｋ溶解させた組成物が、低温の熱処理で硬化する優
れた透明−電極の保農被膜を形成することを見出し、本
発明に到達した。<Means for Solving the Problems> As a result of intensive studies, the present inventors have found that a composition in which a certain terminal hydroxyl ladder polysiloxane and a specific organometallic compound are dissolved in a solvent K is cured by low-temperature heat treatment. It has been discovered that an excellent transparent electrode protection film can be formed, and the present invention has been achieved.
すなわち、本発明は、（ａ》一般式
％式％（１）
（式中、＆および亀は水素または一価炭化水素基、ｎは
正の整数を表す）で示される数平均分子ｔｚｏｏｏ 〜
５Ｇ（ＬＯＯＯの末端ヒドロキシラダーポリイロキサン
、（ｂ）一般式
％式％（）
（式中、Ｍは金属元素、Ｒ′は水素または一価炭化水素
基、ｍは正の整数を表す）で示される有機金属化合物お
よび（Ｃ）溶媒を含有してなる液晶表示素子の透明電極
保護被膜形成用組成物およびこの組、Ｌｅｅ
成物Ｉ透明電極の保護被膜を形成した液晶表示素子Ｋ関
する。That is, the present invention provides a number-average molecule represented by the general formula % (1) (where & and tortoise represent hydrogen or a monovalent hydrocarbon group, and n represents a positive integer)
5G (LOOO terminal hydroxy ladder polyiloxane, (b) general formula % formula % () (in the formula, M is a metal element, R' is hydrogen or a monovalent hydrocarbon group, m represents a positive integer) The present invention relates to a composition for forming a protective film on a transparent electrode of a liquid crystal display element containing the organometallic compound shown above and a solvent (C), and to a liquid crystal display element K on which a protective film of a transparent electrode was formed.
本発明Ｋ用いられる前記一般式（１）で示される末端ヒ
ドロキシラダーポリシロ中サンは、例えば特公昭５８−
５０６５７号公報Ｋ示されているようＫフェニルトリク
ロロシランを、多量の水を用いて加水分解した後、得ら
れた加水分解物をトルエン中でカルボジイミド類を触媒
として脱水縮重合させて得られる。この場合は前記一般
式（１）中の也および−がフェニル基の場合であるが、
本発明においてはこれ以外Ｋメチル基、エチル基等のア
ルキル基、クロルフェニル基等のア−リル基、水素など
とすることができ、これらは分子中Ｋ１種または２種以
上を含むことができる。またこれらの末端ヒドロキシラ
ダーボリア０キサンを混合して用いることもできる。The terminal hydroxy ladder polysilicon resin represented by the general formula (1) used in the present invention K is, for example,
As shown in Publication No. 50657, K phenyltrichlorosilane is hydrolyzed using a large amount of water, and the resulting hydrolyzate is subjected to dehydration condensation polymerization in toluene using carbodiimides as a catalyst. In this case, ya and - in the general formula (1) are phenyl groups,
In the present invention, K may also be an alkyl group such as a methyl group or an ethyl group, an aryl group such as a chlorphenyl group, hydrogen, etc., and these may contain one or more types of K in the molecule. . Further, these terminal hydroxy ladder borea xane can also be used in combination.
末端ヒドロキシラダーポリシロキサンの数平均分子量は
、塗布液としての粘度、硬化性等の点からｚｏｏｏ 〜
ｓｏａｏｏｏｏ範囲であ〕、よシ好ましくは１へ０００
〜５へＯＯＯである。また末端ヒドロキシラダーポリシ
ロキサンの濃度は、その分子量および塗布膜厚Ｋよって
も異なるが、保護被膜形成用組成物Ｋ対して５〜２０重
量％が好ましい。The number average molecular weight of the terminal hydroxyl ladder polysiloxane is determined from the viewpoint of viscosity as a coating liquid, curability, etc.
soaoooo range], preferably 1 to 000
~5 OOO. The concentration of the terminal hydroxyl ladder polysiloxane varies depending on its molecular weight and coating film thickness K, but is preferably 5 to 20% by weight based on the composition K for forming a protective film.
本発明Ｋ用いられる前記一般式（Ｉ）で示される有機金
属化合物としては、Ｔｉ（０π）４． Ｚｒ （ＯＲ）
ａ。Examples of the organometallic compound represented by the general formula (I) used in the present invention include Ti(0π)4. Zr (OR)
a.
Ｔａ （０１％）ｓ 、 Ｉｎ （ＯＲ）ｓ 、 ８１
（ＯＲ）ａ等の化合物がアリ、具体的Ｋｌｄテトライ
ソプロポキシチタン。Ta(01%)s, In(OR)s, 81
Compounds such as (OR) a are specifically Kld tetraisopropoxy titanium.
テトラブトキシジルコニウム、テトラエトキシジルコニ
ウム、ペンタエトキシタンタル、トリプトキシインジウ
ム、テトラエトキシシラン等が挙けられる。これらの化
合物は、前記末端ヒドロキシラダーポリシロキサンの末
端水酸基と反応して８ｉ−０−Ｍなる結合を形成し、低
温で架橋剤としての作用を有する。またその添加ｆｌＫ
よって、形成される保護被膜の屈折率を制御し、透明電
極パターンが点灯していない状態で透けて見えるいわゆ
るネサ黒等の現象を防ぐことができる。これらの有機金
属化合物の添加量は、主Ｋ架橋剤として用いる場合Ｋは
、末端ヒドロキシラダーポリシロキサンのヒドロキシル
基濃度Ｋ対し１０〜１００モルチが好ましく、また屈折
率の制御を主目的とする場合Ｋけ、チタン、ジルコニウ
ム等の有機金属化合物を用い、Ｓｉ原子Ｋ対して金属原
子として１０〜１００モルチとするのが好ましい。Examples include tetrabutoxyzirconium, tetraethoxyzirconium, pentaethoxytantalum, triptoxyindium, and tetraethoxysilane. These compounds react with the terminal hydroxyl group of the terminal hydroxyl ladder polysiloxane to form an 8i-0-M bond, and act as a crosslinking agent at low temperatures. Also, the addition flK
Therefore, it is possible to control the refractive index of the protective film formed, and to prevent phenomena such as so-called Nesa black, in which the transparent electrode pattern is visible through the transparent electrode pattern when it is not lit. The amount of these organometallic compounds to be added is preferably 10 to 100 mole K relative to the hydroxyl group concentration K of the terminal hydroxy ladder polysiloxane when used as a main K crosslinking agent, and K when the main purpose is to control the refractive index. It is preferable to use an organometallic compound such as titanium or zirconium in an amount of 10 to 100 moles of metal atoms per Si atom K.
本発明の組成物は、前記の末端ヒドロキシラダーポリシ
ロキサンを室温またはそれ以上の温度で溶媒に溶解した
後、所定量の前記の有機金属化合物を添加し、攪拌溶解
することＫよって得られる。The composition of the present invention can be obtained by dissolving the terminal hydroxy ladder polysiloxane in a solvent at room temperature or higher temperature, then adding a predetermined amount of the organometallic compound and stirring and dissolving.
この際の溶媒としてＦｌ、Ｎ、Ｎ−ジメチルアセトアミ
ド、Ｎ−メチル−２−ピロリドンブチルセロソルブ、ヘ
キシレングリコール、ブチルセロソルブ等が用いられる
。As a solvent in this case, Fl, N, N-dimethylacetamide, N-methyl-2-pyrrolidone butyl cellosolve, hexylene glycol, butyl cellosolve, etc. are used.
本発明の組成物は、透明電極のパターンが形成された基
板上Ｋ、Ｏ−ルコータ等の印刷機、スピナー塗布機など
Ｋよって塗布し、１００〜３００℃、好ましくは１５０
〜２５０℃のオーブン、ホットプレート等で熱処理し、
透明電極の保護被膜とする。熱処理の時間は、オーブン
の場合は３０〜９０分、ホットプレートの場合は１０〜
３０分程度が好ましい。また。形成される保護被膜の膜
厚は絶縁耐圧の点から５００〜２０００λが好ましい。The composition of the present invention is coated onto a substrate on which a pattern of transparent electrodes is formed using a printing machine such as an O-lu coater, a spinner coater, etc., at a temperature of 100 to 300°C, preferably 150°C.
Heat-treated in an oven, hot plate, etc. at ~250℃,
Use as a protective coating for transparent electrodes. Heat treatment time is 30 to 90 minutes in the oven and 10 to 90 minutes in the case of a hot plate.
About 30 minutes is preferable. Also. The thickness of the protective film to be formed is preferably 500 to 2000λ from the viewpoint of dielectric strength.
（実施例） 以下、本発明を実施例Ｋよシ説明する。(Example) The present invention will be explained below using Example K.
実施例１
Ｎ 末端ヒドロキシラダーポリシロキサンの合成フェニ
ルトリクロロシラン（ＣｓＨｓ８ｉＣ／ｓ）１０５．８
１（ａ５モル）をジエチルエーテル２００ｍｌに溶解し
た。一方２１１の四ツロフラスコＫイオン交換水１１！
を入れ、攪拌機、冷却器、温度計を取りつけ、水浴で２
０℃以下Ｋ冷却し、このフラスコ中Ｋ 上記フェニルト
リクロロシランのエーテル混液を滴下ロートより滴下し
加水分解を行なった。反応温度は２０℃以下とし、４時
間で滴下を終了した。攪拌を止め、二層Ｋ分離した反応
液を分液ロートに入れエーテル層を取シ出した。エーテ
ル層は、イオン交換水で中性Ｋなるまで洗浄した後、無
水硫酸ナ） ＩＪウムＫより一昼夜乾燥した。Example 1 Synthesis of N-terminated hydroxyl ladder polysiloxane Phenyltrichlorosilane (CsHs8iC/s) 105.8
1 (5 moles of a) was dissolved in 200 ml of diethyl ether. On the other hand, 211 Yotsuro flask K ion exchange water 11!
Attach a stirrer, cooler, and thermometer, and heat in a water bath for 2 hours.
The flask was cooled to below 0° C., and the ether mixture of the above phenyltrichlorosilane was added dropwise from the dropping funnel into the flask to effect hydrolysis. The reaction temperature was kept at 20° C. or lower, and the dropwise addition was completed in 4 hours. Stirring was stopped, and the reaction solution separated into two layers was placed in a separating funnel and the ether layer was taken out. The ether layer was washed with ion-exchanged water until neutral K, and then dried over anhydrous sodium sulfate overnight.
その後エーテルを除去し、減圧乾燥器Ｋ入れ６０℃で２
時間乾燥した。得られた白色の粉末はＩＲスペクトルで
３５００ｃｍ−Ｋ−ＯＨの吸収。After that, remove the ether and put it in a vacuum dryer K at 60℃ for 2 hours.
Dry for an hour. The obtained white powder has an absorption of 3500 cm-K-OH in the IR spectrum.
１１３０、１１３５ｃｍ−” Ｋ８ｉ−ＯＳｉの吸収を
示した。その数平均分子量は約１． ｏ ｏ ｏであっ
た。1130, 1135 cm-'' K8i-OSi absorption was exhibited. Its number average molecular weight was about 1. o o o.
次Ｋ前記白色の粉末の加水分解物を還流冷却管。Next, reflux the white powder hydrolyzate in a condenser tube.
攪拌機および温度計を付けた三ツ口フラスコＫ１０９秤
量し、溶媒としてトルエン３０ ｍｌを入れて溶解し、
均一層とした。こ３（Ｃ縮合触媒としてジシクロへキシ
ルカルボジイミド４．１ｇを入れて溶解し、１１０℃で
攪拌還流下Ｋ２時間反応させた。反応容器中Ｋ尿素誘導
体の析出が認められた。反応終了後、反応混合物を放冷
し、尿素誘導体を吸引濾過し、１０体積倍のメタノール
中Ｋ注いでポリマーを析出させた後、濾別し、減圧乾燥
した。得られたポリマーの数平均分子量はｓｏ、ｏｏｏ
であり、またそのＩｎ、スペクトルＫは３５００ｃｍ−
” Ｋ −ＯＨＫよる吸収が見られ、末端ヒドロキシポ
リフェニルラダーポリシロキサンであることを確認した
。Weighed a K109 three-necked flask equipped with a stirrer and a thermometer, added 30 ml of toluene as a solvent, and dissolved it.
It was made into a uniform layer. 4.1 g of dicyclohexylcarbodiimide was added as a C condensation catalyst, dissolved, and reacted at 110°C for 2 hours under stirring and reflux. Precipitation of K urea derivative was observed in the reaction vessel. After the reaction was completed, the reaction The mixture was allowed to cool, the urea derivative was suction filtered, and the polymer was precipitated by pouring K into 10 times the volume of methanol, followed by filtering and drying under reduced pressure.The number average molecular weight of the obtained polymer was so, ooo.
And its In, spectrum K is 3500 cm-
Absorption by K-OHK was observed, confirming that it was a terminal hydroxy polyphenyl ladder polysiloxane.
８）保護被膜形成用組成物の作製および評価上記で得ら
れた末端ヒドロキシポリフェニルラダーシロキサン５ｇ
を、還流冷却管、攪拌機、温度系および滴下ロートを付
けた四ツロフラスコＫ秤量し、溶媒としてＮ、Ｎ−ジメ
チルアセトアミド６０９とヘキシレングリコール３０９
を加え攪拌溶解した。次ｋテトライソプロポキシチタン
の１０重量％イソプロピルアルコール溶液５ｇを滴下ロ
ートから攪拌下Ｋ滴下したのち、室温で約２時間攪拌混
合し、保護被膜形成用組成物を得た。8) Preparation and evaluation of composition for forming protective film 5 g of terminal hydroxy polyphenyl ladder siloxane obtained above
was weighed in a four-way flask equipped with a reflux condenser, a stirrer, a temperature system, and a dropping funnel, and N,N-dimethylacetamide 609 and hexylene glycol 309 were added as solvents.
was added and stirred to dissolve. Next, 5 g of a 10% by weight isopropyl alcohol solution of tetraisopropoxytitanium was added dropwise from the dropping funnel with stirring, and the mixture was stirred and mixed at room temperature for about 2 hours to obtain a composition for forming a protective film.
得られた組成物の濃度は５．１重量１（２０ｏ℃／２ｈ
ｒ乾燥）であり、２５℃Ｋおける粘度は４０センチボイ
ズであった。The concentration of the obtained composition was 5.1 weight 1 (20oC/2h
(dry), and the viscosity at 25° C. was 40 centiboise.
得られた組成物をスピンナを用いてシリコンクエーハ上
に塗布し、１５０℃で１時間の熱処理をし、さらに３０
０℃で１時間の熱処理を行ない。The obtained composition was applied onto a silicon wafer using a spinner, heat treated at 150°C for 1 hour, and then heated for 30°C.
Heat treatment was performed at 0°C for 1 hour.
厚さ２０００λの被膜を形成した。該被膜ｔｃ Ｚ −
のＡ／［［を蒸着し、絶縁破壊電圧を測定したところ、
約１００Ｖの耐圧を示した。A film with a thickness of 2000λ was formed. The coating tc Z −
When A/[[ was deposited and the dielectric breakdown voltage was measured,
It showed a breakdown voltage of about 100V.
次に６４０Ｘ２００ドツトの透明電極パターンを形成し
た３００Ｘ１５Ｇ＋ａｍのガラス基板上に上記組成物を
印刷法で塗布した後、上記同様の熱処理を行ない、厚さ
１０００λの被膜を形成した。Next, the above composition was applied by printing onto a 300 x 15 G+am glass substrate on which a transparent electrode pattern of 640 x 200 dots was formed, and then the same heat treatment as above was performed to form a film with a thickness of 1000 λ.
該被膜上Ｋ８００λのポリイミド系配向膜を形成し、セ
ルを組み立て、電圧印加時の配向状態を観察した。その
結果上下基板の導通による配向不良およびネサ黒は見ら
れなかった。A polyimide alignment film of K800λ was formed on the film, a cell was assembled, and the alignment state when voltage was applied was observed. As a result, no defective alignment or Nesa black due to conduction between the upper and lower substrates was observed.
実施例２
メチルトリクロロシラン（ＣＨｓ ８ ｉ Ｃｌｓ ）
を用いて実施例ＩＡ）と同様の方法で数平均分子量２０
．０００の末端ヒドロキシポリメチルラダーシロキサン
を合成し、これを実施例１と同様のフラ子コ中Ｋ５ｇ秤
量し、溶媒としてＮ−メチル−２−ピロリドン６０９と
ブチルセロソルブ３０ｇを加え攪拌溶解した。さらにテ
トラブトキシジルコニウムのｌＯ重量−ブチルセロソル
ブ溶液５９を滴下ロートから攪拌下に滴下した後、室温
で約２時間攪拌混合して保護被膜形成用組成物を得た。Example 2 Methyltrichlorosilane (CHs 8 i Cls )
The number average molecular weight was 20 in the same manner as in Example IA) using
．． 000 terminal hydroxy polymethyl ladder siloxane was synthesized, 5 g of this was weighed in a flask similar to Example 1, and 609 N-methyl-2-pyrrolidone and 30 g of butyl cellosolve were added as solvents and dissolved with stirring. Furthermore, a solution of 1O weight of tetrabutoxyzirconium in butyl cellosolve 59 was added dropwise from the dropping funnel with stirring, and the mixture was stirred and mixed at room temperature for about 2 hours to obtain a composition for forming a protective film.
得られた組成物の濃度は４．９重量％（２００℃で２時
間乾燥）であシ、２５℃Ｋおける粘度は２０センチボイ
ズであった。The concentration of the resulting composition was 4.9% by weight (drying at 200°C for 2 hours), and the viscosity at 25°C was 20 centivoise.
この組成物の膜特性を実施例１ Ｂ）と同様にして評価
したところ、？、縁耐圧は４５Ｖ／１０００λであり、
セルにおける導通不良、ネサ黒は見られなかった。The film properties of this composition were evaluated in the same manner as in Example 1 B). , the edge voltage is 45V/1000λ,
No conduction defects or black spots were observed in the cell.
実施例３
メチルトリクロロシラン（ＣＨｓ ８１ Ｃｌｓ ）を
用いて実施例ＩＡ）と同様の方法で該平均分子量２ Ｇ
、００ Ｇの末端ヒドロキシポリメチルラダーシロキサ
ンを合成し、これを実施例１と同様のフラスコ中Ｋ５９
秤量し、溶媒としてＮ−メチル−２−ピロリドン６０９
とブチルセロソルブ３０１を加え攪拌溶解した。Example 3 The average molecular weight of 2 G was obtained using methyltrichlorosilane (CHs 81 Cls ) in the same manner as in Example IA).
, 00 G-terminated hydroxypolymethyl ladder siloxane was synthesized, and the K59
Weigh out N-methyl-2-pyrrolidone 609 as the solvent.
and Butyl Cellosolve 301 were added and dissolved with stirring.
この溶液にテトラエトキシシランの２重量％ブチルセロ
ソルブ溶液５ｇを滴下ロートから攪拌下Ｋ滴下した後、
室温で約２時間攪拌混合して保護被膜形成用組成物を得
た。得られた組成物の濃度は４．８重量％（２００℃で
２時間乾燥）であシ。After dropping 5 g of a 2% by weight butyl cellosolve solution of tetraethoxysilane into this solution from the dropping funnel while stirring,
The mixture was stirred and mixed at room temperature for about 2 hours to obtain a composition for forming a protective film. The concentration of the resulting composition was 4.8% by weight (drying at 200°C for 2 hours).
２５℃Ｋおける粘度ｔｉ１８センチボイズであった。The viscosity at 25° C. was 18 centiboise.
この組成物の膜特性を実施例１ Ｂ）と同様Ｋして評価
−したところ、絶縁耐圧は４５Ｖ／１０００λであり、
セルＫおける導通不良は見られなかった。 −
（発明の効果）
本発明の液晶表示素子の透明電極保護被膜形成用組成物
によれば、簡便な塗布法で、しかも低温の熱処理によっ
て硬化し、透明電極のシート抵抗値が上昇−しない優れ
た透明電極保護被膜を形成でき、上下基板の導通Ｋよる
配向不良やネサ黒等を防止できる。When the film properties of this composition were evaluated using K in the same manner as in Example 1 B), the dielectric strength voltage was 45V/1000λ,
No conduction defects were observed in cell K. - (Effects of the Invention) The composition for forming a transparent electrode protective film of a liquid crystal display element of the present invention has the advantage that it can be applied easily, is cured by low-temperature heat treatment, and the sheet resistance value of the transparent electrode does not increase. It is possible to form a transparent electrode protective film, and to prevent poor alignment, blackness, etc. due to conduction between the upper and lower substrates.
＝％ −，−＼き=% −，−\ki
Claims (1)
基、ｎは正の整数を表す）で示される数平均分子量２，
０００〜５００，０００の末端ヒドロキシラダーポリシ
ロキサン、 （ｂ）一般式 Ｍ（ＯＲ′）ｍ（II） （式中、Ｍは金属元素、Ｒ′は水素または一価炭化水素
基、ｍは正の整数を表す）で示される有機金属化合物お
よび （ｃ）溶媒 を含有してなる液晶表示素子の透明電極保護被膜形成用
組成物。 ２、請求項１記載の組成物で透明電極の保護被膜を形成
した液晶表示素子。[Claims] 1. (a) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the formula, R_1 and R_2 are hydrogen or a monovalent hydrocarbon group, and n represents a positive integer.) The number average molecular weight 2,
000 to 500,000 terminal hydroxy ladder polysiloxane, (b) general formula M(OR')m(II) (wherein M is a metal element, R' is hydrogen or a monovalent hydrocarbon group, m is a positive A composition for forming a transparent electrode protective film of a liquid crystal display element, comprising an organometallic compound represented by (representing an integer) and (c) a solvent. 2. A liquid crystal display device in which a protective coating of a transparent electrode is formed using the composition according to claim 1.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20034088A JPH0213A (en) | 1987-10-13 | 1988-08-11 | Composition for forming protective film for transparent electrode of liquid crystal display element |
| EP88309467A EP0312280A3 (en) | 1987-10-13 | 1988-10-11 | A composition for forming a coat for protecting transparent electrodes for liquid crystal display elements |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62-257527 | 1987-10-13 | ||
| JP25752787 | 1987-10-13 | ||
| JP20034088A JPH0213A (en) | 1987-10-13 | 1988-08-11 | Composition for forming protective film for transparent electrode of liquid crystal display element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0213A true JPH0213A (en) | 1990-01-05 |
Family
ID=26512121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20034088A Pending JPH0213A (en) | 1987-10-13 | 1988-08-11 | Composition for forming protective film for transparent electrode of liquid crystal display element |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0312280A3 (en) |
| JP (1) | JPH0213A (en) |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62296839A (en) * | 1986-06-16 | 1987-12-24 | Toshiyuki Oota | Special cake |
| US5245457A (en) * | 1991-04-04 | 1993-09-14 | Sharp Kabushiki Kaisha | Forming a topcoat for liquid crystal display devices having plastic substrates using UV light and temperatures less than 200° C. |
| US5608362A (en) * | 1993-04-15 | 1997-03-04 | Murata Manufacturing Co., Ltd. | Piezoelectric filter using LiTaO3 substrate |
| KR100715681B1 (en) * | 2005-12-06 | 2007-05-09 | 한국전자통신연구원 | Apparatus and method of ubiquitous context-aware agent based on sensor networks |
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| EP3112981A1 (en) | 2015-06-30 | 2017-01-04 | Hitachi Maxell, Ltd. | Power supply control mechanism, electronic device including the same, hearing aid, and power supply control method |
| TWI683039B (en) * | 2014-08-13 | 2020-01-21 | 韓商東進世美肯股份有限公司 | Manufacturing method of transparent electrode and transparent electrode laminate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5095086A (en) * | 1990-08-08 | 1992-03-10 | General Electric Company | Scuff-masking coatings for glass articles |
| DE19804388C1 (en) * | 1998-02-04 | 1999-05-06 | Fraunhofer Ges Forschung | Liquid crystal polysiloxane barrier coating |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5562427A (en) * | 1978-11-06 | 1980-05-10 | Hitachi Ltd | Liquid crystal display device |
-
1988
- 1988-08-11 JP JP20034088A patent/JPH0213A/en active Pending
- 1988-10-11 EP EP88309467A patent/EP0312280A3/en not_active Withdrawn
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|---|---|---|---|---|
| JPS62296839A (en) * | 1986-06-16 | 1987-12-24 | Toshiyuki Oota | Special cake |
| JPH0413975B2 (en) * | 1986-06-16 | 1992-03-11 | Toshuki Oota | |
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| DE112018000271B4 (en) | 2017-01-20 | 2021-12-09 | Panasonic Intellectual Property Management Co., Ltd. | Imaging device |
| DE112017007352B4 (en) | 2017-03-29 | 2021-12-23 | Mitsubishi Electric Corporation | Drive control device |
| DE102017117667B4 (en) | 2017-08-03 | 2021-11-18 | Semikron Elektronik Gmbh & Co. Kg | Power semiconductor module with a pressure device acting on a switching device |
| DE112017007916B4 (en) | 2017-10-11 | 2021-11-04 | Mitsubishi Electric Corporation | OPERATING INPUT DEVICE |
| DE102021108696A1 (en) | 2020-05-11 | 2021-11-11 | Toyota Jidosha Kabushiki Kaisha | Fuel cell system and method for controlling the fuel cell system |
| DE102021108994A1 (en) | 2020-05-22 | 2021-11-25 | Makita Corporation | PORTABLE MACHINING DEVICE |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0312280A3 (en) | 1990-05-09 |
| EP0312280A2 (en) | 1989-04-19 |
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